This game has a large deck of oblong cards and a fairly simple map of provinces in Renaissance Italy. The object of the game is to acquire four connected provinces. Game play is fairly simple as players use numbered cards to get the highest bid for a given territory. Unlike standard auctions, in which only the highest bidder loses their bid to the "bank", in Condottiere, every player loses their bid. Players are, in effect, bidding the number of troops they are willing to lose to win the territory. However, several special effect cards shake the contests up and keep the players guessing.

The newer version (FFG) has a much smaller box, standard-sized cards, slightly tweaked rules, new card abilities and a lower price.